using Mac OS X 10.6.8 I´ve wonderd if there is some way to create a playlist on my R1. Itunes does not support the R1 and while using MSC-Mode there is no way to create a playlist. There are some scripts who sync itunes with the R1 but they only create m3u lists, which aren't support by the R1.

So after the 3rd coffee I found this little free, open source tool: XNJB

XNJB is able to communicate between itunes and the R1 and to add, delete and edit playlists while the R1 is in MTP Mode.

To sync an Itunes playlist with the R1 you can use this script: iTuneMyWalkman